#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/68/2206890.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2206890
loop_
_publ_author_name
'Xiu-Zhi Xu'
'Mei-Jin Lin'
'Jun-Dong Wang'
'Nai-Sheng Chen'
'Jin-Ling Huang'
_publ_section_title
;
 4-[(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]phthalonitrile
;
_journal_coeditor_code           BV6027
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3145
_journal_page_last               o3146
_journal_paper_doi               10.1107/S1600536805027443
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C17 H9 N3 O2'
_chemical_formula_moiety         'C17 H9 N3 O2'
_chemical_formula_sum            'C17 H9 N3 O2'
_chemical_formula_weight         287.27
_chemical_melting_point          550
_chemical_name_common            '4-Phthalimidomethyl Phthalonitrile'
_chemical_name_systematic
;
4-[4-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]phthalonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.0930(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9331(3)
_cell_length_b                   26.2490(13)
_cell_length_c                   10.4901(6)
_cell_measurement_reflns_used    6576
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      54.87
_cell_measurement_theta_min      6.08
_cell_volume                     1356.37(13)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        RAPID-AUTO
_computing_molecular_graphics    'ORTEX (McArdle, 1995)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0737
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11806
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.042P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                1558
_reflns_number_total             3107
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv6027.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206890
_cod_database_fobs_code          2206890
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y-1/2, -z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
O1 0.2424(4) 0.45468(6) 0.53538(16) 0.0646(5) Uani d 1 O
N3 0.6074(4) 0.43376(6) 0.67135(16) 0.0426(4) Uani d 1 N
O2 0.9408(3) 0.43535(6) 0.83339(16) 0.0630(5) Uani d 1 O
N2 -0.0776(5) 0.31120(8) 1.0056(2) 0.0745(7) Uani d 1 N
N1 0.1309(5) 0.17509(8) 0.8964(2) 0.0818(8) Uani d 1 N
H7 0.538(5) 0.6111(9) 0.953(2) 0.073(8) Uiso d 1 H
H9 0.093(5) 0.5598(8) 0.641(2) 0.059(7) Uiso d 1 H
H6 0.808(5) 0.5375(8) 0.950(2) 0.059(7) Uiso d 1 H
H8 0.187(5) 0.6222(10) 0.795(2) 0.081(8) Uiso d 1 H
H4 0.871(5) 0.3810(8) 0.612(2) 0.054(7) Uiso d 1 H
H5 0.583(5) 0.3847(9) 0.525(3) 0.081(9) Uiso d 1 H
H3 0.582(4) 0.2153(9) 0.675(2) 0.057(6) Uiso d 1 H
H2 0.771(5) 0.2870(8) 0.580(2) 0.054(6) Uiso d 1 H
H1 0.317(4) 0.3757(8) 0.7989(19) 0.044(6) Uiso d 1 H
C1 0.3429(5) 0.25312(8) 0.7931(2) 0.0466(6) Uani d 1 C
C2 0.2638(4) 0.30184(7) 0.83024(19) 0.0421(5) Uani d 1 C
C3 0.3708(5) 0.34450(8) 0.7736(2) 0.0426(5) Uani d 1 C
C4 0.5586(4) 0.33982(7) 0.6807(2) 0.0406(5) Uani d 1 C
C5 0.6381(5) 0.29126(9) 0.6455(2) 0.0490(6) Uani d 1 C
C6 0.5322(5) 0.24848(9) 0.7004(2) 0.0537(6) Uani d 1 C
C7 0.2260(5) 0.20910(9) 0.8501(2) 0.0565(6) Uani d 1 C
C8 0.0730(5) 0.30722(8) 0.9279(2) 0.0511(6) Uani d 1 C
C9 0.6713(6) 0.38532(8) 0.6138(2) 0.0485(6) Uani d 1 C
C10 0.4034(4) 0.51094(7) 0.70815(19) 0.0416(5) Uani d 1 C
C11 0.6141(4) 0.50473(7) 0.80021(19) 0.0420(5) Uani d 1 C
C12 0.6674(5) 0.54112(9) 0.8928(2) 0.0551(6) Uani d 1 C
C13 0.5050(6) 0.58403(9) 0.8901(3) 0.0618(7) Uani d 1 C
C14 0.2955(5) 0.59030(9) 0.7978(3) 0.0577(7) Uani d 1 C
C15 0.2404(5) 0.55369(8) 0.7046(2) 0.0509(6) Uani d 1 C
C16 0.3947(5) 0.46518(8) 0.6249(2) 0.0450(5) Uani d 1 C
C17 0.7488(5) 0.45506(8) 0.7767(2) 0.0452(5) Uani d 1 C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C17 N3 C16 111.94(17)
C17 N3 C9 124.89(19)
C16 N3 C9 123.16(19)
C6 C1 C2 118.9(2)
C6 C1 C7 121.4(2)
C2 C1 C7 119.7(2)
C3 C2 C1 120.1(2)
C3 C2 C8 120.42(19)
C1 C2 C8 119.50(19)
C2 C3 C4 121.0(2)
C2 C3 H1 118.8(13)
C4 C3 H1 120.3(13)
C3 C4 C5 118.5(2)
C3 C4 C9 122.34(19)
C5 C4 C9 119.1(2)
C6 C5 C4 121.2(2)
C6 C5 H2 118.8(13)
C4 C5 H2 120.0(13)
C5 C6 C1 120.4(2)
C5 C6 H3 121.5(13)
C1 C6 H3 118.1(13)
N1 C7 C1 178.6(3)
N2 C8 C2 179.6(3)
N3 C9 C4 114.01(18)
N3 C9 H4 110.2(13)
C4 C9 H4 107.9(13)
N3 C9 H5 107.9(14)
C4 C9 H5 105.4(14)
H4 C9 H5 111(2)
C15 C10 C11 121.8(2)
C15 C10 C16 130.1(2)
C11 C10 C16 108.11(18)
C12 C11 C10 121.0(2)
C12 C11 C17 130.8(2)
C10 C11 C17 108.11(18)
C11 C12 C13 117.6(2)
C11 C12 H6 120.6(15)
C13 C12 H6 121.8(15)
C12 C13 C14 121.4(2)
C12 C13 H7 120.2(15)
C14 C13 H7 118.4(14)
C13 C14 C15 121.3(2)
C13 C14 H8 120.0(15)
C15 C14 H8 118.6(15)
C10 C15 C14 116.9(2)
C10 C15 H9 124.3(13)
C14 C15 H9 118.7(13)
O1 C16 N3 124.1(2)
O1 C16 C10 130.0(2)
N3 C16 C10 105.91(18)
O2 C17 N3 124.4(2)
O2 C17 C11 129.6(2)
N3 C17 C11 105.92(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C16 1.202(2)
N3 C17 1.391(3)
N3 C16 1.401(3)
N3 C9 1.450(3)
O2 C17 1.207(3)
N2 C8 1.137(3)
N1 C7 1.130(3)
C1 C6 1.390(3)
C1 C2 1.398(3)
C1 C7 1.436(3)
C2 C3 1.386(3)
C2 C8 1.435(3)
C3 C4 1.386(3)
C3 H1 0.91(2)
C4 C5 1.390(3)
C4 C9 1.507(3)
C5 C6 1.378(3)
C5 H2 0.98(2)
C6 H3 0.95(2)
C9 H4 0.99(2)
C9 H5 1.01(3)
C10 C15 1.380(3)
C10 C11 1.390(3)
C10 C16 1.484(3)
C11 C12 1.377(3)
C11 C17 1.490(3)
C12 C13 1.382(3)
C12 H6 0.89(2)
C13 C14 1.387(4)
C13 H7 0.98(2)
C14 C15 1.388(3)
C14 H8 0.99(3)
C15 H9 0.97(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3 H1 O2 1_455 0.91(2) 2.47(2) 3.275(3) 148.4(17)
C6 H3 N2 2_654 0.95(2) 2.60(2) 3.280(3) 128.6(16)
C15 H9 O1 3_566 0.97(2) 2.44(2) 3.378(3) 160.7(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128830
